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Naphthopyran carbazone derivative as well as preparation method and application thereof

A technology of naphthopyranocarbazone and its derivatives, which is applied in the field of naphthopyranocarbazone derivatives and its preparation, can solve the problems of poor water solubility, complex synthesis process, limitations, etc., achieve high sensitivity, simple synthesis method, selective effect

Inactive Publication Date: 2018-08-10
HENAN POLYTECHNIC UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the existing ratiometric fluorescent probes for copper ions have complex synthesis processes and poor water solubility, which limits their practical applications.

Method used

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  • Naphthopyran carbazone derivative as well as preparation method and application thereof
  • Naphthopyran carbazone derivative as well as preparation method and application thereof
  • Naphthopyran carbazone derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Synthesis of Naphthopyranocarbazone Derivatives

[0032]

[0033] Dissolve 2.10g of 3H-naphtho[2,1-b]pyran-2-carbaldehyde in 100mL of ethanol, then add 0.90g of carbazide, stir under reflux under normal pressure for 1.5h, cool to room temperature, a large amount of solids are precipitated, reduce After pressure filtration, the filter residue was washed with ethanol to obtain a yellow solid which was the target product, and the yield of the target product was 86%.

[0034] Adopt nuclear magnetic resonance instrument to carry out nuclear magnetic resonance analysis to the naphthopyranocarbazone derivative that makes, the result is as follows:

[0035] 1 H NMR (400MHz, DMSO-d 6 ),δ(ppm):10.78 / 10.52(s,1H,NH),8.16-8.21(s,1H,Ar-H), 8.09 / 8.02(s,1H,C-H),7.76-7.88(m,3H, Ar-H),7.55-7.64(m,2H,Ar-H+NH),7.38-7.44(m,1H,Ar-H),7.13-7.19(d,1H,Ar-H),5.23 / 5.18( s,2H,CH 2 ),4.15(s,2H,NH 2 ), see the specific NMR spectrum figure 1 ;

[0036] Mass Spectrum: ESI-MS: m / z=283.1156 fo...

Embodiment 2

[0038]Dissolve 4.20g of 3H-naphtho[2,1-b]pyran-2-carbaldehyde in 200mL of ethanol solution, then add 1.80g of carbazide, reflux and stir for 2h under normal pressure, cool to room temperature, a large amount of solids are precipitated, reduce After pressure filtration, the filter residue was washed with ethanol to obtain a yellow solid, which was the target product, and the yield of the target product was 90%.

Embodiment 3

[0039] Example 3 Naphthopyranocarbazone Derivatives Determination of Optical Properties of Copper Ions

[0040] The naphthopyranocarbazone derivatives prepared in the above example 1 were used as fluorescent probes in DMSO / H 2 In O(0.5 / 99.5,v / v) medium, the molar concentration is 2×10 -5 mol / L solution, respectively, at a molar concentration of 1×10 - 5 mol / L Ag + , Al 3+ , Ca 2+ , Cd 2+ ,Co 2+ , Cr 3+ , Cu 2+ , Fe 3+ , Hg 2+ , K + , Mg 2+ , Mn 2+ , Na + , Ni 2+ , Pb 2+ , Zn 2+ Add an equal amount of the above-mentioned fluorescent probe solution in the solution of metal ions, and adopt a fluorescence spectrometer to carry out fluorescence spectrum analysis (excitation wavelength is 385nm) to it respectively, and the fluorescence spectrum diagram of gained is shown in image 3 . pass image 3 It can be seen that the naphthopyranocarbazone derivatives prepared in Example 1 of the present invention are used as fluorescent probes to interact with copper ions, ...

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Abstract

The invention relates to a naphthopyran carbazone derivative as well as a preparation method and application thereof, and belongs to the technical field of organic synthesis. The preparation method ofthe naphthopyran carbazone derivative comprises the following steps of S1, adding 3H-naphtho[2,1-b]pyran-2-formaldehyde into an organic solvent to be dissolved; then, adding carbohydrazide to obtaina mixture; S2, performing backflow stirring reaction on the mixture obtained in the S1 at normal pressure; S3, after the reaction is completed, performing cooling to room temperature; separating out solid; performing reduced pressure filtering; taking filter slag; S4, washing filter slag obtained in the step S3 to obtain the naphthopyran carbazone derivative. The naphthopyran carbazone derivativehas high sensitivity and high selectivity when being used as a ratio fluorescence probe for detecting copper ions, particularly in application of convenient detection of copper ions in cells as a fluorescence probe.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to naphthopyranocarbazone derivatives and their preparation methods and applications. Background technique [0002] Copper ions are widely distributed in cells and body fluids, and directly participate in the growth and development of cells in the body, reproduction, tissue repair, gene transcription, metalloenzyme catalysis, neurotransmission, immune function and other life metabolic processes. Studies have reported that copper ions are closely related to diseases such as Alzheimer's disease and epilepsy. In addition, copper ions have also become important metal pollutants due to the extensive mining and extensive use of copper mines. Scientists have been working on the detection of copper ions in biological and environmental systems using selective fluorescent sensing probes. [0003] In recent years, fluorescent molecular probe technology has become an imp...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/92C09K11/06G01N21/64
CPCC07D311/92C09K11/06C09K2211/1088G01N21/643G01N21/6445G01N21/6486
Inventor 王元吴伟娜赵晓雷王碗碗
Owner HENAN POLYTECHNIC UNIV
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